


The Truth About Perfection

by thelonelywriter



Series: 30 Day OTP NSFW Challenge [3]
Category: Supernatural
Genre: Alternate Universe - High School, Anal Fingering, Anal Sex, Bottom Castiel, Car Sex, First Time, Impala Sex, Kissing, M/M, Rough Kissing, Teenage Castiel/Teenage Dean Winchester, Top Dean
Language: English
Status: Completed
Published: 2015-07-12
Updated: 2015-07-12
Packaged: 2018-04-08 21:46:58
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,313
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4321923
Author URL: https://archiveofourown.org/users/thelonelywriter/pseuds/thelonelywriter
Summary: <blockquote class="userstuff">
              <p>Dean paused before speaking. "Have you ever thought of taking it, you know, further?" he asked hesitantly. Castiel shifted, looking up at Dean with big blue eyes. </p><p>"Are you asking to take my virginity?" he asked straightforwardly. Dean choked a bit, blushing bright red, and spluttering out a response.   </p><p>"Um, well, kinda. Yes. But, Cas, I only want to take it as far as you want to go, I don't want to push you," he explained. "It's just, well, I really love you, Cas, and I want to be even closer to you," he murmured, fiddling with his fingers as he spoke.</p>
            </blockquote>





	The Truth About Perfection

**Author's Note:**

> This hasn't been beta'd so please don't kill me for plot holes, grammer errors, and mistakes galore! Also, the challenge for today was, 'First time,' so here's what I did with it :3

Dean's thoughts buzzed as he pulled Castiel closer to him on the worn couch that sat across from the TV in his living room. Castiel let out a soft purr that had Dean smiling as he kissed the top of Castiel's head, lingering for a moment. Then, he sighed, dropping his head. "Cas?"

"Hm?" Castiel answered simply. Dean paused before speaking.

"Have you ever thought of taking it, you know, further?" he asked hesitantly. Castiel shifted, looking up at Dean with big blue eyes. 

"Are you asking to take my virginity?" he asked straightforwardly. Dean choked a bit, blushing bright red, and spluttering out a response.

"Um, well, kinda. Yes. But, Cas, I only want to take it as far as you want to go, I don't want to push you," he explained. "It's just, well, I really love you, Cas, and I want to be even closer to you," he murmured, fiddling with his fingers as he spoke.

Castiel smiled softly because he knew Dean wasn't always good with feelings, and he wasn't always good with saying what he felt, but Cas could tell he was trying. The teenager had to admit that he had thought about it before, but he was shy about the topic. Not until Dean brought it up.

Castiel could tell that Dean was a bit nervous, and Cas knew he was too, but he figured that a few juniors in high school could manage losing their virginity. It was Dean, after all, he would never hurt Cas, he would make it special. "You want this?" Castiel asked Dean, and Dean nodded in response. Castiel smiled, kissing Dean softly. "My house is empty at six on Friday. You can come over if you want," Castiel proposed, nuzzling softly into Dean. Dean grinned widely, stroking over Cas' hair.

"I'd be glad to."

\---

Castiel sighed as he threw his stuff down on his bed with a sigh, following it with his own body, plopping down with it. It was Thursday. Tomorrow was Friday. He was nervous, of course, but he didn't regret his decision one bit. He wanted this, he had for a while. But the fear of messing up, of being inadequate, had him by the stomach, and was twisting it. But the calming thought of Dean, Dean who loved him, who wouldn't judge him, was enough to calm his nerves.

He was in the middle of thinking when someone knocked on his door. "Come in," he sighed, and the door opened before he finished his words.

"Hey little bro," Gabriel said, and Castiel rolled his eyes, sitting up to look at him.

"What do you want, Gabe?" he inquired, and Gabriel grinned.

"Wanted to let you know that you and your little lovebird won't be getting any tomorrow, I'm inviting Kali over," he boasted, and Castiel blushed.

"How did you know that we-" Castiel began, and Gabriel dismissed him with a wave of his hand.

"You aren't very sneaky, Cassie, not when you steal my condoms and lube," Gabriel remarked, raising an eyebrow. Castiel looked down, blushing.

"Gabe, I invited Dean over first," Castiel complained. Gabriel just shrugged, walking over to ruffle Cas' hair.

"Sorry baby bro, older ones get the rule of the house. And you're only seventeen," he whispered, smiling before walking away. 

As he closed the door, Gabriel called out, "But tell me when you become a real man!" Castiel grit his teeth, shutting his eyes. Time for Plan B.

\---

"Dean, there's a problem," Castiel spoke into the phone. On the other line, Dean laid languidly on his bed, playing idly with a rubix cube.

"Oooh, is this like phone sex?" he asked playfully. Castiel pinched the bridge of his nose, pacing his room.

"No, Dean, we're not having phone sex," Castiel replied, sighing.

"Disappointing," Dean grumbled as he sat up on his bed, placing the rubix cube aside.

"Can we use your house, Gabriel took ours over," Castiel questioned, biting his lip. Dean froze, thinking of what was going on tomorrow at his house. He swore under his breath, and Castiel let out an urgent, "What?"

"Sammy is having Jess over so both my parents are gonna be home," he voiced, and Castiel sighed.

"Are there any other options?" Castiel inquired, and Dean thought hard, racking his brain for something. Then, he grinned widely, because there was another option he hadn't thought of.

"I'll tell my Dad that I'm taking a ride somewhere, I'll pick you up, then we can have sex," Dean proposed. Castiel quirked an eyebrow, his pacing ceasing.

"Sex. In the Impala. Dean, is that all you can come up with?" Castiel questioned. Dean rolled his eyes. 

"Listen, Cas, we don't have to do this now. If you wanna do it some other time, or even spontaneously, then that's fine, it's not like tomorrow is the one and only day for us to fuck for the first time," Dean told Castiel. 

"Gay sex isn't exactly _spontaneous,_ Dean, you have to, you know, prepare," Castiel said quietly. Dean then furrowed his eyebrows because that brought them to an unanswered, important point.

"Whose bottoming anyways?" he asked, and Castiel blushed bright red on the other line. 

"I kind of, well," Castiel began, but the words weren't coming out, so he spit them out. "I want your dick inside of me," he blurted out. Dean choked, it now being his turn to blush.

"I thought you said this wasn't phone sex," Dean croaked. Castiel chuckled a bit on the other line.

"Dean, I want to do this, and I'm ready to do this. So if the only place we can fuck is your car, then we'll flail in the backseat together. It won't be perfect, but that's alright," Castiel reassured. Dean smiled, and nodded softly on the other end. Even if it was car sex, even if it was their first time, they would be together, and that's what really mattered.

\---

Castiel walked down the stairs hurriedly, seeing Dean's car out in the driveway. He ran his fingers through his hair, turning around to grab something off the table. "Have fun losing your virginity," Balthazar stated calmly from where he was rummaging in the fridge. Castiel turned bright red, blinking over at him.

"Did Gabe tell everyone in the friggin' house?" Castiel grit out. Balthazar smirked.

"Pretty much," he responded, and Castiel groaned. He would never hear the end of this.

"I'm leaving," Castiel declared, turning on his heel, and walking away.

"Don't forget to tell us how it went," Balthazar quipped as Castiel shot him the finger, and walked on and out the door.

When he got in Dean's car he sighed a breath of relief at the familiar smell of leather, and the memories of the times they would fool around in it. Dean smiled over at Cas, giving him a sweet, short kiss. "So, where do you wanna go?" Dean questioned as he put the car in drive, and they began their little journey. Castiel grinned, because he had just the place in mind.

"That little alcove, you know by that desolate road. You can see all the stars there. That was the first place we kissed, remember?" Castiel inquired to find Dean grinning and nodding his head in response.

"Have I ever mentioned that I love your ideas?"

"Yes, but I like hearing it again," Castiel replied with a grin.

"I also love some other parts of you," Dean declared in a voice that had dropped a bit lower. Castiel grinned even more, looking over at Dean.

"Really?" Castiel asked simply, and Dean glanced over at him with a smirk.

"You'll find out a little bit more when we stop the car," Dean told him with a waggle of his eyebrows.

\---

The ride there felt like a million years to each teen, though it was truly only twenty minutes. Once they got there it was only slightly awkward, unknown touches detracted, longing looks, and talk of past times, or of the stars. Finally, Castiel just sighed, taking Dean's hand in his. "Kiss me," he said softly, and Dean looked him in the eye, those deep blue eyes, and slid closer to him.

Dean cupped one side of Castiel's face, bringing their lips together softly and sweetly, just as they always did before class, or when parting ways, or at each other's houses. It was simple, an invitation to more, one that Castiel initiated, and Dean took up. Castiel ran his tongue gently over Dean's lip, and Dean opened, his own tongue delving into Cas' mouth, his fingers unconsciously pressing down unto Castiel's head a bit harder.

Castiel felt the adrenaline that had already been flowing through him intensify as the kiss did, and Cas' tongue was making precise movements, and his hands were gripping Dean's sides. Soft moans of appreciation were echoed from Dean to Castiel, their bodies growing hot with want, with anticipation. Dean canted one leg over Cas' thigh, straddling him so that they were even closer. Castiel nipped softly at Dean's lip before Dean was pulling away, lips ghosting Cas' jawline, teeth grazing the sensitive pulse points of his neck.

An impatient Castiel slid his hands up the back of Dean's T-shirt, encouraging him to take it off. Which he did, but struggled with, and Castiel couldn't help but chuckle. "Don't chuckle at me, I'm trying my best," Dean grumbled, and Castiel drew him in for a deep kiss.

"You just look cute when you fumble around like that," Castiel murmured, nipping at his collarbone. 

"Well, lemme' see how cute you look when you fumble around," Dean whispered with a smirk. Castiel gave Dean another kiss before he took off his own shirt, throwing it aside. Dean's hands found his waist, smoothing over it. "I'd say you look even cuter than me," he said quietly, moving down to kiss up and down Castiel's bare chest.

Castiel grabbed at Dean's back, bringing him close as Dean rocked his hips down, and each boy groaned softly at the friction. Castiel rocked his hips back up, and Dean pressed an open mouthed kiss to his shoulder. "Backseat?" Dean simply questioned, and Castiel nodded, watching Dean struggle even more to crawl over and into the backseat. Castiel did the same, landing on top of Dean with an, 'Omph,' followed by a little chuckle as Dean smiled wide beneath him.

The kisses grew frantic, messy and open mouthed as Dean sucked marks onto Cas, ones that Cas didn't even care that he would have to cover up. Castiel rolled his hips down particularly hard at one point, and Dean pulled away, panting. "Socks, shoes, pants," Dean stated, and Castiel dropped his head down unto Dean's chest. 

"This is gonna be a real bitch, you know that?" Castiel mumbled, still pressing kisses to Dean's chest. Dean smoothed a hand through Cas' hair with a smile, already toeing off his shoes and socks.

"We can manage, don't worry, babe," Dean remarked as Castiel kicked off his socks and shoes, proceeding to sit back on his heels, undoing his jeans and sliding down his boxers with them, revealing his hardened cock. Dean bit his lip at the sight, watching Cas grunt and struggle as he finally threw his jeans and boxers into the front seat.

Dean did the same, sighing as his dick finally got some form of release. Castiel stared lustfully down at him, and Dean smirked. "View must be pretty nice from up there, huh, babe?" he teased, also throwing his pants and boxers aside. 

"Oh, shut up," Castiel told him, yet with a soft smile, draping himself over Dean once again. 

Their cocks met as Dean planted one foot on the floor of the car, and sparks flew throughout both of them. Dean moaned underneath Cas, who was rocking his hips down, fingertips pressing into Dean hard enough to make bruises. The feeling of pleasure built and built, and Castiel got so lost in it that he forgot the whole purpose of their little meetup; until Dean brought it up. "Cas," he breathed into the sloppy kiss they were sharing. Castiel simply hummed in response, adrenaline filling him up. "You brought lube and condoms, right?" Dean asked urgently. Castiel's hips slowed as he groaned in annoyance, not wanting the pleasure to cease, yet still nodding, knowing that there would be greater pleasure ahead. He groped on the floor, finding his pants, and taking out the small bottle of lube and a condom. Dean took them in his hands, and for a moment they just stared. Then, Castiel cracked a smile, nudging Dean.

"I'm all yours now," he whispered, sending chills up Dean's spine. 

"And you're sure about this, you want this?" Dean inquired. Castiel scooched forward, giving Dean a soft kiss.

"I do, I can promise you that I do," Cas replied, and Dean smiled. 

"Alright, how do you wanna do this? What position works?" Dean questioned. Castiel bit his lip, thinking hard before grinning.

"Here," he began, laying on his back and throwing one leg over the front seat, taking the other up to his chest. "Does that work?" he asked. Dean looked him over, licking his lips before nodding.

"This definitely works," he replied, and Castiel chuckled.

"Alright, hurry it up, I'm dying over here," Castiel said, and Dean laughed, popping open the bottle of lube. He poured a generous amount on a single finger, scooting closer to the space between Castiel's legs. He pressed a finger down slowly to his entrance, and Castiel hissed.

"Does that hurt?" Dean asked, scared of hurting Cas. Castiel scoffed, shifting a bit where he lay.

"No, your finger is just really fucking cold," Castiel explained, and Dean responded by slowly circling the ring of muscle, warming the lube up and relaxing Castiel.

"Are you ready?" Dean asked, and Castiel nodded. Dean let his fist hang lightly around Cas' dick, just to ease the likely unpleasant feeling there would be at first. He pushed one finger in slowly, his other hand using a nice and steady rhythm that had Castiel moaning. "How're you doing?" Dean asked after he had slid his middle finger in and out multiple times.

"I'm fine, Dean. It feels a little weird, but a good kind of weird," Castiel commented, and Dean nodded, waiting a minute or two before he slipped in a second one, adding even more lube.

Dean was just about to ask where Cas was at with the two fingers, when Castiel let out a piercing moan at a certain thrust of Dean's fingers that had electricity shooting through him. His foot also came unhooked from the front seat and hit Dean in the side of the head. "Dean! Oh my God, are you okay?" Castiel questioned, propping himself up on his elbows to get a look at Dean, who was rubbing his head with the hand that was previously wrapped around Cas' cock. Dean just looked down at Cas and sighed, shaking his head.

"I swear to God, Cas, you're so lucky that you're sexy as fuck..." Dean said with a little smile. 

"I'm so sorry Dean, shit, I just, you hit my prostate and it felt really- Jesus, Dean!" Castiel yelped as Dean hit it again unexpectedly. This time, however, Castiel had repositioned his leg, so that meant no more kicks to the head for Dean. 

"I'm guessing that this feels good," Dean said with a little smirk, hitting that spot with his fingers over and over. Castiel let out a shaky groan, his hips twitching into the sensation.

"You have no idea," Castiel panted, getting used to the sensation, the pleasure running through him, mixing with adrenaline still coursing in his veins. 

Dean made sure to take good care of Cas, smoothing a hand over his thigh, giving soft nips and licks to his skin, making sure he was doing okay. "Third one?" he asked after a few minutes, and Castiel nodded furiously, repositioning, and stilling as Dean slowly pushed in a third finger. "How's it feel?" Dean asked softly, and Castiel focused on the feeling. It felt strange, but it felt good, filling in a weird way.

"It feels... good. Keep going," he responded, and Dean smiled, kissing the inside of Cas' thigh, sucking a bruise as his fingers kept working, and Castiel waited until he felt ready, until he was keening and throwing his head back. "Dean," he panted. Dean looked down at him, and his dick took great interest in the sight of Castiel coming that undone. 

"You ready?" Dean asked softly. Castiel looked him in the eye and nodded. 

He pulled his fingers out, and Castiel whimpered at the loss, but quieted when Dean hovered over him, giving his a soft, deep kiss. He smiled before pulling back, and grabbing the condom with shaky hands, ripping it open, and slipping it on before grabbing the lube. He sighed, assessing their position, figuring how it would work. 

Castiel's legs were spread, so Dean moved closer, throwing one leg over Castiel's bent one, and positioning the other one behind himself so he was kneeling over Cas. He applied a generous amount of lube, and looked down at Cas, who nodded before Dean slowly pushed in halfway. 

The two were breathing heavy, not talking, not until Cas gave him the go ahead to push deeper. This time Dean pushed in inch by inch until he was flush against Castiel. Castiel wiggled around a bit, getting used to the feeling. It was strange being so full, feeling Dean so close. But it was arousing, and when Dean made the first shallow thrust, Castiel began to get the hang of it. "God, you're so beautiful, Cas, so fucking beautiful," Dean breathed out, and Castiel groaned.

"You don't know how good you feel Dean, fuck, just like that," Castiel moaned when Dean brushed his prostate.

The angle was awkward, and each boy would slip occasionally, uttering a chuckle. The car was steamy, the windows were fogged up, and no, it wasn't perfect, it was far from it, not in a cramped car with skin sticking to leather seats. But it was enough, it was perfect to them. 

Dean's pace was speeding up and Cas was breathing slack jawed, lost in the pleasure, feeling just the right kind bubbling up inside of him as he looked up at Dean who was desperately reaching out to touch Cas, to grab at him and feel him because they were there together, they were closer than ever, and it drove each of them wild. "Dean," Castiel groaned. "Fuck, I'm close," he panted. Dean huffed out a breath of laughter, thrusting only harder.

"Trust me, I'm right there with you," Dean said through gritted teeth. Then, Dean gave a particualuraly hard thrust, and Castiel was waiting for another one, babbling out pleas and curses until Dean hit the same spot, and Castiel was coming all over his stomach with Dean's name on his lips. 

Dean thrusted his hips a few more times before his head was thrown back in ecstasy, and his nerves were buzzing with pleasure.

The air held still as the pleasure washed away, left with only a sort of high that felt like heaven to each of them. When Dean pulled out, Castiel winced a little, and Dean leaned forward, kissing Castiel hungrily as Castiel matched it with a passion. When the two pulled back, still partially out of breath, Dean grinned. "Pretty good for losing our virginity in a car, huh?" he asked. Castiel chuckled, nodding.

After Dean and Castiel got dressed, they laid under the stars as they had years ago. Their fingers interlaced, hearts beating in time, Dean pressed a kiss to Cas' temple. "I love you, Cas," he whispered, and Castiel smiled, drawing Dean in for a real kiss.

"I love you too, Dean."

**Author's Note:**

> Annnd, as always tell me what you thought!! And thank you so much for reading :) (Sorry this is a little late posting, I won't always be able to post everyday)


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